Wigs, Google, and a Venture Anti-Portfolio

Most venture firms have mental lists of deals that they shoulda/coulda done, but didn’t, and yet only a vanishingly small number of such firms will ever list the deals that got away. After all, it makes you look intermittently dumb and human and risk-averse, and gunslinging venture sorts could never concede any of those things to be true.

Trust the iconoclasts at Bessemer, however, to maintain at least a partial public list — they call it their “anti-portfolio” — of the deals that got away:

Bessemer Venture Partners is perhaps the nation’s oldest venture capital firm, carrying on an unbroken practice of venture capital investing that stretches back to 1911. This long and storied history has afforded our firm an unparalleled number of opportunities to completely screw up.

While, over the course of our history, we did invest in:

– a wig company – a french-fry company – the Lahaina, Ka’anapali & Pacific Railroad

We chose to decline the investments below, each of which we had the opportunity to invest in, and each of which later blossomed into a tremendously successful company.

Google[BVP partner David Cowan’s] college friend rented her garage to Sergey and Larry for their first year. In 1999 and 2000 she tried to introduce Cowan to “these two really smart Stanford students writing a search engine”. Students? A new search engine? In the most important moment ever for Bessemer’s anti-portfolio, Cowan asked her, “How can I get out of this house without going anywhere near your garage?”

[Update] I’m particularly fond of reading that BVP passed on Federal Express seven times. That takes real pig-headed moxie to miss out on FedEx so many times — and even more moxie to tell people later.